


Stan's Dick Diaries

by Taeters



Category: South Park
Genre: 16-17, ;DD, Aged-Up Character(s), Anal Fingering, Anal Sex, BDSM, Blood Kink, Bottom Eric Cartman, Bottom Stan Marsh, But consensual, Cock Slut, Consensual But Not Safe Or Sane, Consent is Sexy, Explicit Language, Explicit Sexual Content, Friends With Benefits, M/M, Masochism, Voyeurism, but yall already know the drill, change my mind, tags added as story progresses, they're juniors so like
Language: English
Status: In-Progress
Published: 2019-10-01
Updated: 2019-11-21
Packaged: 2020-11-01 11:00:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 13,244
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20814023
Author URL: https://archiveofourown.org/users/Taeters/pseuds/Taeters
Summary: At 3 in the morning, Stan Marsh woke in a start, drenched in a cold sweat. He suddenly had an epiphany, realizing what he really, really needed in life was one, two, maybe three or four or more dicks.So, he did what any other perfectly illogical dumbass would do; he messaged the two sluttiest people in school.OR:Stan gets slut advice and fucks every guy in his grade. Every. Single. One.





	1. The Steps to Whoredom

**Notes for the Chapter:**

> Much like Stan, I woke up in a cold sweat at 3 am a couple of nights ago. I immediately thought to myself, 'wow, what if Stan was a cock slut?'  
And thus this fic was born!
> 
> Obviously, Stan won't be fucking EVERY boy in his class because some are just way too obscure to do, but I'll do all the mains (yes, including Timmy and Jimmy, because we stan inclusion) and maybe some more minor characters like Kevin Stoley or Pete Thelman. Stan's asshole is about to be WRECKED!
> 
> This fic will always update as soon as possible! I'll strive for once every week, but it might end up being once every other week. I might develop a posting schedule for myself to keep me more motivated and on task.
> 
> Anyways, I hope all you horny bitches out there enjoy my work!!! I know I'll enjoy writing it!
> 
> Also, HERE'S TO SEASON 23!!!

** _Stan Marsh _ ** **added ** ** _Kenny McCormick_ ** ** and ** ** _Bebe Stevens_ ** ** to a chat.**

Stan Marsh: Hey guys

Stan Marsh: so

Stan Marsh: Uh

Stan Marsh: I’m gay

Kenny McCormick: *surprised pikachu*

Kenny McCormick: whaaaaaat 🤯🤯🤯 no way. what a turn of events

Bebe Stevens: its 3 am

Kenny McCormick: anddd?

Kenny McCormick: ur still up tho??

Bebe Stevens: haha guilty

Stan Marsh: guys no im

Stan Marsh: Im being serious

Kenny McCormick: rlly?

Stan Marsh: y. Yeah i’m.. pretty sure.

Kenny McCormick: well DAYUM

Kenny McCormick: 🥳💃 CONGRATS!!!

Bebe Stevens: well, that’s great

Bebe Stevens: buuttt… why r u telling me of all ppl?

Kenny McCormick: yea I mean lowkey confused

Kenny McCormick: i thought u would’ve told ur bff kyle first

Stan Marsh: well

Stan Marsh: The thing is

Stan Marsh: I need advice. help

Stan Marsh: and i thought you two would be the best option

Bebe Stevens: advice? from these bitches??? not sure if that’s the best choice, but go off

Kenny McCormick: yea

Stan Marsh: Well i

Stan Marsh: I want some dick

Kenny McCormick: WOAH HELLO STANLEY

Bebe Stevens: oh man what a damn mood

Kenny McCormick: stanothy, what has brought upon this sudden… urge?

Kenny McCormick: not that either of us has room to judge but i’m curious

Stan Marsh: uhhhaahh welll…

Stan Marsh: Okay, this is gonna sound really fucking stupid, but,

Stan Marsh: so I had this dream last night. It was _ crazy_, i had boys all over me, like, touching me, kissing me, licking me, dicks EVERYWHERE and i think i creamed myself, like, 5 times bc when I woke up i was a _ mess, _and yet I _ still _ had a hard-on

Stan Marsh: It was probably the most intense dream I’ve ever had. I haven’t ever had a dream about a girl like that, but the dream I had tonight was just the most intense dream of all the dreams i’ve had of being fucked by guys

Kenny McCormick: damn, i think i creamed my pants just thinking about that

Bebe Stevens: imagine having a wet dream so good it makes you realize ur sexuality

Stan Marsh: I’m obviously not, like, 100% positive but…

Stan Marsh: remember how wendy and i broke up, like, a couple weeks before school ended?

Kenny McCormick: ohhhhh my god

Stan Marsh: Yeah. it was a mostly mutual thing, but i initiated “the talk” and we both kinda said “look, you’re awesome, but the spark just isn’t there anymore. Also our sex sucks.”

Kenny McCormick: LMAO

Stan Marsh: I kinda just wanted to break up with her so I could explore my, like, curiosities?

Kenny McCormick: im pretty sure shes a lesbian now?

Stan Marsh: **what**

Bebe Stevens: im guilty for that 😉

Bebe Stevens: we fucked a couple days after you guys broke up and i guess i turned her 🥺🥺

Kenny McCormick: bebe,

Bebe Stevens: I KNOW i know that’s not how it works im just joking

Bebe Stevens: anyways, stan the man, what advice were you looking for?

Stan Marsh: Well, you two are the biggest sluts i know

Bebe Stevens: thank u

Kenny McCormick: aw thats so sweet 🤗😘

Stan Marsh: so i want help becoming a slut

Bebe Stevens: YEAHH THAT’S WHAT IM FUCKIN TALKING ABOUT

Kenny McCormick: ive been waiting for this day my whole life

Stan Marsh: I wanna go into junior year becoming a new, confident, sexy stan marsh that can get any guy I want with just a bat of my eyelashes.

Stan Marsh: so.. Can I get your help?

Kenny McCormicK: duh

Bebe Stevens: hell fuckin yeah.

* * *

Date: 08/13

Entry #1

The Making of a WHORE!!!

_ Okayy, so… hey. This is the beginning of my diary, journal, w/e you wanna call it, idrc. Kenny fondly refers to it as my “dick diaries,” so whatever lol. _

_ Kenny and Bebe had the genius idea for me to start a sex diary, and of course I naturally jumped on board, drooling at the idea of being able to reread every sexual encounter I’ve had. We established that the goal is to fuck every guy that I know in our grade at least once by the end of the school year, which is like, okay, bet, let’s fuckin do this. _

_ This first entry is just about the process I took over the summer with Kenny and Bebe on my way to becoming a stupid spoiled whore, so take that as a hint, future horny Stan. _

_ Anyways. _

_ 1: The first step to whoredom I took with Kenny and Bebe is a few changes in appearance. _

* * *

“Ow, ow ow ow ow ow ow ow _ow, fuck_,” Stan complained, trying his very hardest to not squirm in his seat as the lady across from him attacked his bellybutton with a needle. “Bebe, what the fuck, how did you handle getting one of these?”

She shrugged, glancing up from her phone as she took a video. “I’m a bad bitch, I guess.”

The lady stabbing Stan quickly snickers, finishing up his piercing with a simple but cute silver belly button ring that held a clear jewel on both ends. “Alright: finished.”

Stan momentarily looked down, admiring the metal now embedded in his skin, before standing up to fully see himself in the full-length mirror. He had to admit, the shiny jewelry looked… pretty damn cute. It was a simple little thing, but it perfectly accentuated his belly button that was only a little bit chubby. He couldn’t help but grin a bit upon seeing his new appearance.

“Damn, Stan, you look hot!” Kenny exclaimed, Bebe feverishly nodding beside him.

“You rock that better than me,” Bebe winks, still recording on her phone. “You’ll get every man in school.”

Stan smiled wider at his reflection. “You really think so?”

“Hell yeah!” Kenny smiles back, accentuating his point with a slap to Stan's ass, leading Stan to blush.

“Okay, so, after this, we’re gonna go shopping,” Bebe informs, her phone now put away. “We’ll buy you some cute new rings for when you can change it later. We’ll get you a haircut, because…” she looked at Stan’s hair with a grimace. “Who cuts your hair? Your dad?”

Stan pouts. “No. I just… haven’t really gotten a haircut in a while.”

She toys with Stan’s hair for a moment. “Figures. Want any highlights? Pink, maybe, so we can match?”

“No. My dad _ would _ then try to shave my hair off.”

“I think we should stick with the shaggy look,” Kenny pipes in. “Works wonders for me.”

“I agree. But less greasy and more controlled.”

“What if we do a cute, messy fringe?”

“Yes! That would be so hot!”

“Wait, guys-”

“No complaining,” Bebe scolds. “You need a haircut. Anyways, so once we’re done here, we’ll get you a haircut, buy some new belly rings, maybe other jewelry- you still have your ears pierced, right-?” he nodded, “-okay, yeah, and we’ll buy you some new clothes, too. Not saying that your clothes aren’t _great,_ but…” she grimaced again.

“Your clothes need to be more extra,” Kenny explained. “Crop tops, booty shorts, all the shit.”

“I mean. Okay, that’s great, I appreciate all the effort you’re putting into me, but just _ how _are we gonna afford all this?”

Bebe only smirked. “Daddy’s credit card. He couldn’t care less.”

“Oh my _God,_” Kenny groans. “You really are a stupid, spoiled whore.”

She shrugged. “It works, right? Anyways, Stan,” she says, turning back to me. “Ready for the tongue now?”

Stan felt a little queasy at the idea, but it’d be a waste to spoil the two for $30 deal, so he only nodded. They both grinned back.

“I’m gonna warn you; these hurt like Hell. But you’ll be fine!”

Stan gave Kenny a glare as he sat back down on the chair, waiting for the lady to murder his tongue. Kenny really did have a way with words, huh?

* * *

_ The tongue did end up hurting way more, but I can’t lie, it also looked pretty hot lol _

_ We bought almost, like, an entire new wardrobe for me, along with my new haircut, and with all these new changes I looked like a new, totally hot person. _

_ So then, 2: Second, Bebe and Kenny taught me some tips and tricks on how to come across sexier. _

* * *

“_Mmmnn_… God, _ yes~ _” she moaned out, breaths coming out in strangled intervals, and almost as soon as she started, it was over. “Okay. You try.”

“Mm… mmn?” Stan tried, but sounded a lot more like a dying walrus instead of the sex Goddess Bebe presented herself to be. She deadpanned.

“Okay- maybe that was too much. I know you’re probably shy, but I want you to give me, like, one deep, cute, _guttural moan_ from the _pit of your being._ Just pretend that we’re not here! Close your eyes and let one rip,” she kindly encouraged. Stan smiled at her, feeling strangely comforted.

“Okay, I’ll try the best I can.”

Stan closed his eyes. He blocked out the gentle breathing of his two friends, ignoring when they shifted on the bed. He thought of something besides how pressured he felt, thinking back to the dream he had. The dicks, mouths, bodies of all those men, filling up his senses, and he felt himself bite his lip in the real world. His thoughts built up, and he suddenly heard himself release the biggest, loudest, _neediest sound_ he’d ever heard in his life, unconsciously thrusting his hips forward.

He bashfully snapped his eyes wide open, looking upon the star-struck faces of his two friends.

“_Damn._ I’m wet.”

Kenny nodded his agreement. “I’m sailing at half mast right now.”

“That was amazing!” Bebe exclaimed, now much more enthusiastic. “Whatever you did to elicit such a sexy moan, keep working at it. Remember: practice makes perfect!”

“Precisely. Now, Stanothy, I wanted to teach you something myself, but it’s a little… erm… invasive? More sexual than what we’ve been working on today. Are you alright with that?”

To the surprise of Kenny, Stan eagerly nodded his head. “Yeah! Teach me everything you think is important! What is it, anyways?”

“Stretching,” Kenny says, matter-of-factly, which clearly just confuses Stan. He snickers. “Oh, yeah: I forgot you’ve been living your whole life a sad, straight boy. Basically, I need to stick my fingers up your ass and teach you how to do it yourself, show you your prostate, etcetera, etcetera.”

A jolt went through Stan’s body at Kenny’s words. _ What the fuck did he just say_? Stan understood nearly nothing that Kenny just said, most confusing words being ‘prostate’ and ‘stick my fingers up your ass.’

“I-I. Okay…?”

“Are you okay with me doing that?”

Stan had never even thought that that was a part of the gay sex process, but it made more and more sense as he thought about it. Assholes are pretty Goddamn tight. Expecting a dick to naturally fit inside seemed to be completely irrational, so Stan slowly nodded at Kenny. He didn’t seem to be completely satisfied with this answer, so Stan croaked out a “yes,” more confident this time.

Kenny grinned. “Okay; then take your pants off and lay down. Bebe, hand me some lube.”

Bebe, now on her phone, seemingly not at _ all _phased by the conversation at hand, blindly reached into her bedside table without a single glance up. She pulled out a bottle of lube, tossing it to Kenny who murmured a quick “thanks.”

When Kenny turned back to Stan, he was surprised to see Stan already half-naked, lying down, legs spread just a bit. He was quite obviously flustered, blushing and hiding half his face with a hand. He left on his oversized sweater, his belly ring peeking out only just a bit from under the hem.

“God… you really are pretty, Stan,” Kenny complimented as his eyes raked over him. Stan turned an impossible shade of red. He couldn’t find it in him to say anything in response.

And as Kenny began to lean down, smirk playing his lips, he couldn’t control the thoughts of _wow, oh God, holy fucking shit, this is happening, why didn’t I notice how hot Kenny was before?_

“So-” Kenny spoke, interrupting Stan’s thoughts “-I’m just gonna stimulate you a bit. I won’t enter yet, but I’ll lick and massage your hole, okay?”

Stan nodded again, breathing a “yes,” and a new thought interrupted the old ones that _oh fuck, my asshole is probably dirty as H- _

But then Kenny started lapping at his hole, and all Stan could do was strangle a gasp at the foreign sensation. It felt… pretty much what it sounds like; somebody licking your asshole. But everything down there is just so _ sensitive _ that even a few licks to his hole gave Stan the chills. He licked up, down, around, stimulating and simultaneously relaxing Stan as he melted into the soft touches as he stared transfixed down at Kenny with laboured breaths.

Before he knew it, a new sensation joined his tongue as he gently prodded a finger at Stan’s hole. He kept licking as a lubed finger poked at him and Stan’s head was swimming. He eventually (unfortunately) pulled his mouth away, leaving Stan feeling a bit empty, but the wet finger massaging his puckered hole still felt pretty damn nice.

After a little bit of that, Stan heard the bottle of lube snap open again, and felt more cold liquid coat his anus and Kenny’s finger.

“Okay. I’m gonna slide it in now. It’s gonna hurt a bit but mostly just feel weird and uncomfortable, especially since this is your first time. But I promise it loosens up and starts to feel _ really _fuckin’ good, especially once I find your prostate. Are you okay? Are you ready? Still feeling up to it?”

Stan felt like he couldn’t talk. The words ‘first time’ rang through his head a couple of times and he suddenly felt like a blushing virgin once again, awkwardly rolling around with Wendy in her bedroom. But still Stan nodded before remembering that’s not enough for Kenny, trying his hardest to strangle out a “yes.”

Then Kenny just went for it, and _ holy shit _ he was right. That felt fucking _ weird_ and burned a lot. It almost felt like taking a really huge shit, but like, backwards, and that was a disturbing enough image to say the least.

Stan felt himself tensing around Kenny, and suddenly Kenny’s tongue was back again to help Stan relax once more. It was a weird mix of pain and pleasure that he didn’t know how to feel about, but it definitely wasn’t _ bad_. Just weird, a bit uncomfortable, but apparently it was supposed to get better.

Before he knew it, Kenny’s finger was somehow _ all the way inside his asshole_, and that thought was weird but also a bit of a turn on, as Stan was stretched to fit Kenny as much as possible. And just as he thought he might have finally been getting used to the weight inside him, Kenny started _ moving. _ The burning discomfort was back again: not as prevelant as before, but still definitely there and making him squirm.

As Kenny worked his (really, quite small and bony) finger inside Stan with expertise, the burning slowly started to die down and now it was starting to feel _ good_. Stan couldn’t help the little gasps and mewls he released through the stimulation, and he vaguely registered Bebe cheering him on for his good moans- he almost completely forgot she was there.

“Okay, adding another finger,” Kenny called, and before he could ask any questions Stan was already responding with an airy “_yes_.”

Kenny added a second, lubed finger and the strange discomfort was back, but Stan expected it and the pleasure from the first finger nearly outweighed the pain. Stan became accustomed to this finger a lot quicker than the first, and this time Kenny scissored them apart, _ stretching _ Stan’s hole wide.

That felt weird, but also pretty damn good. Stan was starting to realize that he had an affinity for being stretched and filled. He almost began to crave more once the scissoring became normal and complete pleasure with no discomfort.

“I’m only going to do two fingers, since it’s your first time, but the more fingers the better, really,” Kenny spoke, and his voice was hoarse which was hot as _ fuck. _ Stan moaned in response and Kenny smirked. “Fingering yourself is probably something you’ll wanna practice on yourself at home. It’s a pretty good idea to pre-stretch yourself before going out to see someone, just to save a bit of time, but it’s really up to you,” he shrugged. “Now, let’s just see if I can find that prostate…”

Kenny began harshly thrusting in and out, changing his position every time, apparently in search of something. Stan vaguely remembers him saying something about finding something, but he could hardly register Kenny’s words as each thrust sent him closer and closer to the edge, moaning louder and louder, and-

“_Fuck_!” he practically screamed. “_Fuck, fuck, fuck, shit, right there, _ oh my _ God_, Kenny~!”

Kenny grinned. “Bingo.”

Now Kenny was absolutely _ pounding _ Stan’s nerves with his fingers, and Stan couldn’t contain or control anything he was doing or saying. His legs spread wider and wider, he spilled garbled words and noises from his mouth, he grabbed onto the sheets for _ dear life_, and finally he felt the familiar swell of heat in the pit of his stomach.

“_Kenny_, oh fucking shit, I’m gonna-!”

And as if he couldn’t feel any better, Kenny wrapped his hand around Stan’s dick, pumping as fast he could. A shit-eating grin played at his lips.

“Come for me, baby,” he whispered through hooded eyes, and that was fucking it.

Game over.

His legs twitched as he orgasmed, white spurts of cum shooting from his dick, staining his _ brand new fucking sweater _ but, obviously, Stan was too caught up in the euphoric feeling to even think about that right now. He kept his eyes shut tight, moaning loud and long as he thrust up into Kenny’s hand and rode out the last blissful waves of his orgasm.

Stan could swear he almost felt ringing in his ears as he realized _ holy shit_, _ that was the best orgasm I’ve ever had in my life. _

“Aw, shit, now I got cum all over my bed,” Bebe complained, to which Kenny just rolled his eyes.

“As if that’s something new to you,” and Bebe just laughed, because she knew that was nothing but the absolute truth. “Anyways, holy fuck. Stan is _ hot _,” he spoke, looking back down at the boy recovering from his Earth-shattering orgasm. “Really sensitive, too. For sure definitely a natural slut,” and Bebe nodded an agreement. “Anyways, I got a major stiffie now, could you give me a blow? I’ll eat you out.”

“Fuck ye-”

“_Wait_,” Stan croaked, and Kenny raised a pierced brow.

“Hey, cutie, what’s up? You doing alright? Do you need anything?” Kenny asked, and it was amazing how thoughtful he was even with a hard dick.

“Let me suck your dick,” Stan said like the cock hungry slut he was slowly becoming.

“Woah- wait, holy shit, are you sure?”

Stan feverishly nodded. “This can be another learning tool, right? Sucking dick must be a major part in all of this, so, y’know, practice makes perfect,” Stan said, trying to flirt his best with a subtle wink.

Kenny just stared at him for a few long moments. “Well, when you put it like that…” he smirks. “How could I possibly say no?”

And as Stan and Kenny go for round two, Bebe sighs, looking down at her phone once again. “Fine. Just leave my pussy here to suffer.”

* * *

_ That training day was pretty intense. Kenny got me off, I got Kenny off, then Kenny got Bebe off, but I think I learned sum stuff _

_ After that, I went home and practiced fingering myself for hours on end, and it slowly became generally easier and I can find my prostate pretty damn quick now. I also learned how 2 moan really good, how 2 bat my eyes, how 2 bite my lip and wink without looking like I’m dying, how 2 appear confident (which is sexy), and how 2 successfully flirt!!! So, like, SCORE!!!!!!! _

_ 3: Kenny and Bebe helped me find some products to up my sex appeal (that aren’t necessarily clothes) _

* * *

“This one, and this one, and this one, and this one, and-”

“Bebe, do I _ really _ need this many toys?”

“Absolutely.”

“Stanothan, if you’re actually planning on eventually taking a dick up the ass, you need to practice with the thickness of dicks of _ all _ shapes and sizes,” Kenny informs.

“_Omigod_,” Bebe suddenly squealed. “This is absolutely _ gorgeous_.”

She pulled something from a hanger off the wall, and in her hands was an absolutely _ explicit _ piece of lingerie. It was white, two pieced, tight in some spots but flowy in others. It was lacy and very obviously see-through, veils of white extending down from the top piece. It came with two thigh-high stockings that could attach and detach to the bottoms, and overall it just looked like something a very sexy angel would wear.

“Oh my lord,” Stan said, trying to sound exhausted but more so just coming across star-struck.

“Cute, right?” Bebe fawns. “I might have to buy one for myself…”

“Hey, how about this?” Kenny piped up a few feet away, pulling out a Goddamn _ virgin killer sweater. _

“Adorable!” Bebe squealed again before running away, continuing to collect and grab various pieces of toys and lingerie.

At the end of the trip, they ended up buying _ lots _ of toys- dildos, vibrators, plugs, cock rings, even the more kinky toys like handcuffs and whips that Stan was increasingly more and more concerned about how he was gonna hide -then three pieces of lingerie: the angel lingerie, the virgin killer sweater, and that cat lingerie that’s famous in Japan, and finally they bought _ way _too many thongs.

Stan was worried about the strain they were causing on Bebe’s dad’s credit card, but when he asked she just told him to ‘not worry about it.’

* * *

_ It’s been a real struggle to hide all this shit from my parents, but I’ve managed. They think that the clothes n my new piercings are weird but they’re fine lolol _

_ Overall, I’ve been thru it a LOT this summer. I’m not about 2 pretend it wasn’t fun/enjoyable, because it was. I can’t even count on both hands how many times Kenny and I fooled around. He gave me hella orgasms, but I just feel kinda bad 4 Bebe bc she was always left out lol _

_ School starts in about a week and I’m rlly nervous, not even boutta front. Like- idk. It’ll just be an all out different experience than what I usually go thru cuz, like, I’m just a different person now??? And I have my new style and everything so I’m worried that everyone’s gonna judge me???? But I have my new BFFs Kenny and Bebe now, so it’s okay. _

_ I’m, like, 99% sure that the first person I’ll fuck will be Kenny, so I’ll see you then, future Stan. _

_ \- Stan _🤪

**Notes for the Chapter:**

> AND SO IT BEGINS!!!
> 
> You can probably guess who the star of the next chapter will be, so I hope you Kenny fuckers are gd READY!!! Kudos and comments are greatly loved and appreciated! If you wanna stay updated with the fic, make sure to bookmark and/or subscribe!
> 
> See you next time ;)


	2. Pretty Boy (Kenny McCormick)

**Notes for the Chapter:**

> Here you go you Kenny fuckers

It was about a week after school started that he got the text.

_ Kenny McCormick: ay, u doin anything this weekend? ;) _

Stan felt a sort of shiver run through his body. Is this finally it? Will he finally properly bone Kenny? Finally dicked down? His hands shook just slightly as he shot a text back to Kenny.

_ Stan Marsh: of course not _

_ Kenny McCormick: awesome, wanna come to my house tomorrow? _

_ Stan Marsh: fuck yea _

_ Way to be subtle, Marsh_, he thought to himself, but shook it off as he placed his phone in the car’s armrest box. He started the car, blasting his Nirvana CD already set and loaded, and pulled out of the school parking lot as he thought over the past week.

Monday was _ very _ different from what Stan had usually experienced. He hadn’t worn anything especially provocative, but he had a new, confident, sexy demeanor and everyone could tell. Kyle was mostly used to Stan’s new… _him,_ because they hung out quite often over the summer, but this didn’t stop him from telling Stan he looked hot. Cartman, on the other hand, was a bit more surprised after not seeing him all that often, called him a ‘fag’ and seemingly went silent once he noticed Stan’s tongue. For the rest of the day he could feel subtle stares on him, and he would be a total liar if he said he wasn’t absolutely fucking _ living for it._ A lot of people were also surprised to see how close he was to Kenny and Bebe- especially Bebe -and Stan could practically feel Clyde’s jealous stares from across the cafeteria during lunch. If only he knew…

Tuesday and Wednesday went relatively smooth, normal, but Thursday was when shit hit the fan and Clyde did find out why he had no reason to be jealous.

Stan had told Cartman on Wednesday that he was gay, or at least thought he was. Because even though Stan and Cartman weren’t as close as they had been in elementary or early middle school, he was still one of Stan’s closest and long-lasting friends, so he felt Cartman had the right to know as Kenny, Bebe, and Kyle already knew. He took it… surprisingly well, simply shrugging and saying ‘I knew it’ without much more of a reaction. What he didn’t know, however, was that Cartman would then spend a good part of his night spreading this info to the _ entire class._ Stan knew this to be true the moment that Clyde approached him, asking “is it really true that you’re gay?”

Ah, classic Cartman. Stan then remembered exactly why he no longer talked to Cartman as much as he used to, and almost more infuriating was that when confronted, he did anything but apologize, just shrugging once again and saying “you never said I couldn’t.”

Which… was true, but Stan also somehow had a suspicion that even if he explicitly told Cartman not to tell anyone else, he still would. Besides, it just the fucking priciple of the damn thing!

So, Thursday was a surprise, as he wasn’t expecting nor nearly ready to be outed to the entire school, but Stan couldn’t say he was entirely angry. It had saved him the trouble of having to tell anyone himself, and over the summer Kenny and Bebe had helped him learn to better love himself. So, yeah, it was kinda shitty, but it was junior year and he kinda just didn’t give a fuck anymore.

Friday was less chaotic than Thursday, but still filled with stares and questions from people who caught on late. But, being completely honest, he kinda loved the attention.

Still, he was beyond thrilled that the weekend was _ finally _ at hand. As much as he loved seeing his friends, everything got exhausting between waking so early, being forced to go somewhere he didn’t wanna go to learn things he didn’t want to learn and to see people he didn’t want to see; by the end of the week, he was barely hanging on, and he could really use a beer.

Luckily for Stan, he was already home, parked on the side of the street for God knows how long. He went inside, not so discreetly grabbing a beer, and beelining it to his room. He took a few sips and already felt better, the tension seeping out of his shoulders. He also realized just how absolutely tired he was, and after he slugged off his backpack and set his beer on his desk, he crashed into his bed. His thoughts slowly went to Kenny.

God, tomorrow couldn’t come soon enough.

* * *

“Yo,” Kenny casually greeted, opening the door. Stan immediately noticed their difference in appearance; Kenny stood in front of Stan plad in Iron Man sweatpants and a plain white t-shirt, while Stan stood in front of Kenny with a cropped sweatshirt revealing his piercing and borderline booty shorts. He even threw on a bit of mascara and eyeliner for good measure, but suddenly he felt embarrassed for being overdressed. Kenny raised his brows. “Damn, you look hot.”

Stan felt his face get warm. “Yo. Uh, thanks.”

Kenny ushered Stan through his house, though Stan has been there about 1 million and 5 times, especially in recent.

“Where are your parents?”

Kenny shrugged. “Out. No idea, honestly.”

Stan frowned. Even after all these years, his family life had stayed just as bad, worsened if anything. However, these thoughts selfishly get pushed from Stan’s head as he entered Kenny’s room to see Bebe sitting on the floor.

_Oh._

“Oh,” he spoke aloud. “Hey.”

“Stanie, why do you sound so disappointed to see me?” Bebe inquired. Bebe had picked up the annoying quirk from Kenny to add “Stan” to the beginning of every name.

“I’m not!” Stan said, trying to sound a lot more cheerful.

“I think he thought we were gonna fuck,” Kenny said. His tone sounded almost… condescending? Stan immediately faltered.

“I-”

“I mean, we totally are.”

Stan jumped at this, looking at Kenny in utter bewilderment. “_What_!?”

“Well, you wanted to, right? Quite frankly, I think I would feel quite offended if I was the only one you didn’t fuck.”

Stan’s mouth went dry. “Well- I- I mean-” Stan pointedly looked at Bebe.

“Ohh, is that the problem?” Kenny asked as if this wasn’t one of the most awkward situations Stan had ever been in. “Well, we’re best bitches, right? We’ve all fooled around in front of each other so I thought it would be fine. I wasn’t gonna invite her in the first place, but she said she ‘didn’t wanna feel left out,’” he mocked. Bebe stuck out her tongue.

“We’re stupid, spoiled, and whore! I wanna see stupid and spoiled fuck for the first time!”

“Wait- who’s who?” Kenny asked.

“Stan is spoiled, you’re stupid.”

Stan couldn’t help but snicker. “Uh… no, you’re definitely the spoiled one.”

“I gotta say, I agree with Stanley on this one.”

Bebe scoffed. “Fine. But Stan doesn’t have _ nearly _ enough experience to be whore.”

“I think it’s fitting for Stan to be stupid. He’s the biggest dumbass of us three, honestly.”

Stan just nodded.

“Okay, but, Stan, really… I can, like, go, if you want me too?”

“No!” Stan bursted, surprising himself. “No, you’re right. Y’all really are my best bitches. Stay, you horny bitch.”

Bebe wickedly smiled. “Well… if you _insist,_” she said as she lied onto the ground.

Kenny turned away from them both. “Alright, well, I’m gonna order some pizza. Get the Wii set up and let’s play some Mario Kart!”

So for the rest of the night they played Mario Kart and Just Dance on Kenny’s shitty old Wii, eventually collapsing together in a pile on the floor, exhausted and coughing their lungs out but still laughing. Their breath mingled together in a garlic, pizza scent and Bebe accidentally knocked over a can of Dr. Pepper with her foot, but they were too lost in their laughter to care.

Stan felt Kenny wrap his arms around him and immediately his heart-rate skyrocketed. All he could see was blonde: the blonde from Kenny’s head resting in the crook of his neck and Bebe’s messy curls bouncing as she began to realize the mess she made.

“Hey big boy,” he mumbled, and Stan just kind of laughed at the strange nickname.

“Hey.”

“Look at _meee,_” he whined, and Stan laughed again before turning around.

Kenny and Stan met eyes, and God _ fuck _ Stan just couldn’t believe how pretty he was. His blue eyes were light and always held a twinkle of optimism despite even the roughest times, and that’s something Stan had always admired about Kenny because it was always something he could never do himself. Kenny’s face was littered with gentle freckles, adding to his boyish charm along with his only slightly crooked teeth. You’d think this would be ugly, but he always tried to maintain his teeth the best he could, even resorting to stealing toothpaste when they ran out and didn’t have enough money to buy more yet. Stan once asked why Kevin got the privilege of having braces while he didn’t, and Kenny had told him that “those dumbasses never planned for having two more children, so Kevin always got to have things Karen and I never did because he was the first child. Usually it’s the last child to get spoiled, and I wish that was the case because Kevin is kind of a dick. Karen deserves a lot better.”

Kenny was also incredibly skinny and quite short after being malnourished, and sometimes it looked like you could snap him like a twig. He’d eaten nearly a whole pizza when the two boxes arrived and neither Bebe or Stan even thought about trying to stop him, and he had to pay with almost all of his saved money. It made Stan quite sad sometimes, and yet he acted as though he had all the energy in the world and exuded _ total top energy._

“What are you thinking about, pretty boy?” Kenny whispered.

Stan licked his lips. “How pretty _ you _ are.”

Stan saw Kenny quick glance down to his lips and back up. “Yeah?”

Now Stan’s eyes went to Kenny’s lips, but they parked there. “Yeah.”

This time Kenny smirked, his white, crooked smile, and then he was leaning in and Stan leaned as well. Stan felt their breaths hotly intermingle for two quick seconds, smelling the weed and pizza from his mouth, before their lips finally met.

And it quickly dawned on Stan that he and Kenny had never actually kissed before.

They wasted no time licking into each other’s mouths, and it was _ really _ like no other kiss he’d had before. Unlike now, the only other kisses he’d had were with girls, mostly Wendy. They were, y’know, _okay,_ but this? Stan felt like he couldn’t get enough. He wanted nothing more than for Kenny to devour him whole, to drown in the taste of weed and pizza and Mountain Dew, a Katy Perry song playing on loop in the background.

Stan registered the sound of Bebe getting up and leaving the room, presumably to try and find something to clean up the Dr. Pepper with, and while he was distracted by that, Kenny took it as an opportunity to fucking _ lift _ him up and slam him on the bed. Stan made a noise of surprise, surprised that Kenny could even lift him between their weight difference, but Stan refused to part his lips from Kenny’s.

Now under Kenny, Stan looped his arms around Kenny’s neck, kissing him more feverishly than ever. Kenny began to pull away and Stan couldn’t stop the whine that left him, chasing his lips; however, Kenny stopped him with a gentle push to Stan’s chest. He sat up, straddling Stan’s hips.

“Hold on, big boy,” he purred, gently playing with Stan’s belly ring. Stan shivered. His belly hadn’t fully healed, but it no longer hurt, and that felt strangely good. Then again, any touch from Kenny felt good.

He was pulled from his thoughts as he felt Kenny tugging at his shirt. He shifted, allowing Kenny to more easily take it off, and watched as he threw it to the side. He vaguely wondered how many times Kenny had done that exact move, before Kenny was licking at his neck and eliciting a strangled noise from Stan. Kenny breathed onto the wet patch he made on his neck and Stan felt his whole left side tingle, squeezing his eyes and breathing a moan. Kenny raised his pierced brow.

“Sorry,” Stan apologized, “I’m really sensitive on my neck.”

“Isn’t everyone?” Bebe spoke from where she knelt on the floor, and Stan momentarily forgot that she existed and never realized she even came back in the room.

Stan was about to say something in response, but then Kenny bit down on his neck, _hard,_ and Stan could only exhale all the air in his lungs with a moan.

Kenny continued to kiss, bite, and suck his way down Stan’s neck, chest, and stomach, running a tongue along his bellybutton, and by the time Kenny reached his shorts, Stan was painfully hard.

“Oh? What’s this?” Kenny cheekily asked, palming Stan’s erection, leading Stan to moan and stutter his hips.

“Did you seriously just say ‘oh what’s this’?” Bebe snickered.

Kenny only shot her a look, still palming Stan’s strained hard-on, and once he turned back he started to mouth Stan through his shorts. Stan felt like he was in Heaven and Kenny hadn’t even really touched his dick yet, but he longed to have his dick freed.

Then, as if he read Stan’s mind, Kenny began to unzip his shorts. Stan helped Kenny shimmy them off and Kenny went back to teasing Stan through his boxers. If felt a little better, a bit looser, but at the same time this was all going too slow and he just wanted to be rawed _ right now. _

“Y’know, Stan, I must say… I’m a bit disappointed you didn’t wear a nice pair of panties for me,” he frowned, breathing over Stan’s clothed cock. Stan shivered. “I would’ve really loved to see it… and more importantly, loved to tear it off.”

He then punctuated his point by grabbing Stan’s boxers with his teeth, slowly pulling them off and somehow perfectly doing it. Stan lifted his hips, trying to help Kenny as much as possible, and once Kenny threw them off to the side again he came face to cock with Stan’s dick.

“Hey, old friend,” Kenny talked to his dick, then licked a looong stripe from the base of his shaft to the tip. Stan felt a shudder rack through his entire body, living in pure ecstasy.

Suddenly, something seemed to confuse Kenny, and he pulled away with a raised brow. Stan looked up at him with hazy, lustful eyes and ragged breaths.

“Did you stretch yourself before you came?”

Oh yeah. He forgot he did that.

“Y-” he swallowed, suddenly realizing his mouth was full of saliva, “yeah. Took your advice.” He smiled up.

Kenny continued at Stan, something shifting in his eyes that made heat pool in his stomach. He grinned. “You really are becoming a good little slut, huh?”

The words made Stan whine, and Kenny leaned back down to continue his blow. He went on for a good while before Stan warned him that he was about to come, and he pulled away with a string of saliva still connecting his mouth to his dick. Which was pretty hot.

“Bebe, toss me the lube.”

Stan, again forgetting that Bebe existed, watch her reach into Kenny’s drawer and find the bottle of lube without difficulty. She tossed it to Kenny, and Stan noticed her eyes held something similar to Kenny’s- lust, hunger, desire. She felt Stan’s stare and met his eyes. They awkwardly shared a smile.

“You okay, Babes?” Kenny asked as he began to strip his clothes, lube set to the side. Stan looked back up at Kenny, admiring his now naked abdomen. Stan couldn’t help but reach a hand up and feel along his skin, able to clearly feel his ribs and noticing a few light scratches and bruises. Kenny had always been an adventurous boy prone to injury.

“I-” she croaked, then interrupted herself with a cough. “...Can I touch myself?”

“Hell yeah,” Kenny said, without hesitation. Stan looked back over to Bebe and saw her begin to reach a hand into her leggings, but then Kenny started to finger his hole and he moaned. “I jus’ wanna make sure you’re nice an’ stretched,” Kenny slurred, splitting him open with three fingers.

Stan couldn’t say a word, he just deliriously nodded and rode out the feeling of Kenny’s fingers. He glanced to Bebe once, watching her hand move fast underneath her leggings, her mouth open in ecstasy.

When Kenny accidentally brushed Stan’s prostate, he screamed a “_fuck_!” and thrusted back against Kenny’s fingers, until he unfortunately pulled out and left Stan feeling empty. He frowned.

“Don’t give me that look, Stanothy,” Kenny affectionately purred, and it took everything in Stan to not roll his eyes at the nickname. “Now’s the best part.”

Stan, cheeks red, hair mussed, looked down and finally noticed Kenny’s cock. He’d seen it before, after fooling around so often, but now felt like such a different context. That was about to be _ inside of him_, not just in his fist or mouth, but in his _ ass. _ The thought made him drool a bit, and he watched as Kenny rubbed his thick, not-half-bad cock with lube. He lined himself up to Stan’s hole, then looked down at Stan with The Look.

“Stan, are you feeling alright? Are you ready? Are you sure you wanna do this?”

“Yes. Yes, yes, 1,000 times _ yes _ to everything, just please get your dick in me _ now_.”

He smiled. “Good whore,” he purred, running a hand through Stan’s hair. Stan shuddered at this, whining, desperate, lips parted. God, he had never felt this much absolute need in his life before.

And then, Kenny slowly pushed his way into Stan, and Stan gripped the sheets for dear _life._ This wasn’t his first time taking on a length of width or size, not after playing with all the dildos he had, but it certainly _ was _ the first time it was real, warm, pumping with blood and flesh and it just felt all too good and it felt awfully similar to the euphoric feeling of being drunk, and he absolutely _loved it_.

When Kenny’s balls met with Stan’s ass, Stan felt thoroughly stuffed and, once again, absolutely fucking loved it. Ever since the day Kenny had first fingered him, he craved to be filled. At this point he honestly didn’t understand how he ever lived without the knowledge of this mind-numbing pleasure, but now that he knew what had been missing over the sixteen years of his life, he couldn’t possibly get enough. He craved it.

Kenny shivered above Stan, relishing in the feeling of his dick being completely devoured, and he swallowed thickly. “Are you okay?”

“Fuck. _Yeah,_” Stan moaned, still gripping the sheets and looking at Kenny. “Move. Please, God, move.”

And Kenny had not a single snarky remark. His eyes darkened and he began to move, slowly, teasingly, painfully, and Stan tried to help as much as he could by thrusting his hips slowly back. His hands move from the sheets to Kenny, gripping and touching him everywhere he possibly could, before parking on his nipples and giving them a gentle squeeze. Kenny moaned above him, stuttering his hips and beginning to thrust faster than before. _Bingo._

Stan continued playing with Kenny’s nipples, brushing and pinching and twisting, continuously earning moans and praise and making Kenny get more and more frantic, Stan reacting the same. Kenny eventually leaned his head down, biting and licking Stan’s neck, to which Stan nearly cried, and he could vaguely hear Bebe’s moans in the back. Kenny changed his position with each thrust, until finally-

“_Yes! There! Again! Again!_” Stan cried with everything in his being, thrusting as hard as he could against Kenny and clawing at his back.

Kenny continued to pound into the same spot, rendering Stan completely fucking hysterical as slurred speech and moans spill from his mouth. He heard the mixed moans of Kenny and Bebe wonderfully playing as music in his ears, the slapping of skin on skin as Stan and Kenny completely lose their composure, and it was getting to be way too much. He felt the familiar heat pool in his stomach once again, this time intensified by about 56897%.

He tried to warn Kenny by saying “I’m gonna come!” but instead it came out completely garbled, something akin to “I’m- ah- ah- gonn_aahhhh_-!”

Nonetheless, Kenny understood, nodding his head and biting into the crook of Stan’s neck one last time, and that was fucking it.

Game over.

Stan came, hot spurts of white spilling out and staining both their stomachs. He came with a long, exaggerated moan, absolutely blissful after his mind-boggling orgasm, and after a few more thrusts he felt Kenny’s hot seed fill him to the brim. It was another feeling he’d never experienced before, but God_damn _ if it didn’t feel absolutely fucking amazing. He heard a loud moan from Bebe somewhere in the back of his mind.

Kenny collapsed on Stan. They breathed each other’s sweat for a few long moments, Kenny’s now flaccid cock still inside Stan. They shared each other’s heat as they lazily looped their arms around one another.

Then, Kenny slowly pulled out of Stan’s abused hole, Stan cringing and also immediately missing the thickness inside of him as Kenny’s seed started to leak from his ass.

“That… was…” Stan could only breathe.

“Amazing?” Kenny inquired, and Stan aggressively nodded.

Kenny wiped up the pool of cum off Stan’s stomach and, to Stan’s disbelief, just fucking _ licked it up_. It was probably one of the hottest things that Stan had ever seen, and if Stan hadn’t just gotten absolutely wrecked then he probably would’ve gotten a stiffie.

Kenny’s eyes went to Bebe who was breathing hard, seemingly reeling from her own orgasm. “Hey, Babes, get your ass over here!”

Bebe snapped out of her trance, looking up at Stan and Kenny, but hopped up from the floor as soon as she registered what Kenny had said. She squeezed herself in-between Stan and Kenny in Kenny’s tiny full-sized bed, threatening to push Kenny off, but they eventually all settled into a comfortable position, arms and legs wrapped around one another in a messy tangle of limbs.

It didn’t take long for them all to drift to sleep, and Stan relished in the wonderful afterglow of his orgasm in the arms of his best friends.

* * *

Date: 8/26

Entry #2

Pretty Boy

_ So, yeah. Kenny was just as good as I thought he would be. I don’t know if it was the fact that it was my first time having sex with a guy or if Kenny really was that good, or both, but it was hands down the best orgasm I’ve had in my life; as to be expected from the literal sex god himself. _

_ He’s also just, like… so sweet. he always makes sure that I completely 100% consent, which is like, yea, duh, and then he always makes sure that I’m okay and comfortable after we fool around. It’s so sweet & cute I’m :’) _

_ Soo yea, Kenny’s really sexy and that was a GOOD fuck. I’m now 110% sure that I’m gay. 10/10 would fuck again and hopefully will lol _

_ \- Stan 🤪 _

**Notes for the Chapter:**

> I hope you enjoyed! Comments and kudos appreciated!!! See ya horny fucks next time ;)
> 
> Edit: these are the sweatpants kenny was wearing https://m.bonanza.com/listings/iron-man-super-hero-inspired-womens-jogging-pants/656134495?goog_pla=1&variation_id=914530411&gpid=68416460221&keyword=&goog_pla=1&pos=3o14&ad_type=pla&gclid=Cj0KCQjw84XtBRDWARIsAAU1aM3sjX-4wQi_ihzG_Psi-fObAm5Bqlhi5igwoHBgFrDla8miSQhizwkaAh9KEALw_wcB


	3. Stop It. Get Some Help. (Eric Cartman)

**Notes for the Chapter:**

> It's finally fucking UP!!! I know, I know, it's been OVER A MONTH, and I honestly don't have much an excuse for that besides that I've been very busy and this chapter is fairly long!! I know it may be disappointing that after a month of absence that the chapter I return with is Eric Cartman but trust me, if you give it chance, I think you'll like it.
> 
> In other news: life has been slowing down again for me lately, so I should be able to get to (fairly) regularly posting again! Yay!! If you find that this chapter isn't really your cup of tea (which would be understandable because it's FAIRLY intense) then do not fear, there will be plenty of other fucks and kinks in the future!
> 
> That being said, I hope you enjoy! It's certainly not perfect and has only been formerly beta-read like, once, but I worked hard and like it, so I hope you do too!

“I really think your best bet will be Kyle,” Bebe said to Stan. They- Stan, Bebe, and Kenny -lied down, sprawled across the floor of Bebe’s room. Bebe held Stan’s right hand, coating his fingertips with a glossy pink, while Kenny sat just off to the side with a blunt in hand. “That boy’s honestly so whipped for you it would be easy to get him to follow along.”

Kenny agreed. “He may be a bit vanilla- Hell, he’s probably still a virgin, but it would be easy to get in his pants. He also has a _ nice _ ass.”

“No,” Stan immediately shut down. “No, absolutely not. That’s my _ best friend_, guys, I can’t just… exploit him like that.”

“So… wait, are you saying that you’re just gonna exclude Kyle from your dick diaries?” Kenny asked.

“No, I guess it’s just… different. Like… I dunno, nevermind.”

“No, no, no, you _ have _ to say it now,” Bebe said.

Stan looked between Kenny and Bebe. Bebe had stopped painting Stan’s nails, although they very clearly weren’t finished, and Kenny had put out what very little was remaining of his blunt. They both earnestly stared at Stan, and he felt helpless under their looks. He had no choice but to spill his guts.

“I honestly think… that… I might like Kyle?”

Silence. Kenny and Bebe stared at Stan in utter silence.

“I knew it,” Kenny and Bebe said in unison.

“No. You did not.”

“Stanothan, you’re really obvious, and even worse than that you’re really damn oblivious. You’re almost completely unaware of your own feelings, nonetheless Kyle’s. I’m pretty sure I know you better than you know yourself,” Kenny said.

Stan furrowed his brows. “That’s not true.”

Kenny rolled his eyes. “_Please_. I, and about the rest of the entire fucking class, know that you’ve been in love with Kyle since the 7th grade, and him to you as well.”

“Kyle isn’t in love with me.”

And to that they both barked out a laugh.

“You’re funny,” Bebe said, then finally continued to paint his nails.

Stan furrowed his brows again. “Can we get off of this topic?”

Kenny snickered. “Right, right. Well, Stanley, who do _ you _wanna fuck first? Or, I guess… next?”

“I don’t know! That’s why I’m asking you guys! I’m still a new whore, so I need help,” he frowned to Kenny.

Kenny hummed, placing a finger on his chin. He tapped a few times. “Well… Stan, I’m gonna say somebody, but I’m not sure if you’ll be entirely happy with who it is?”

Stan felt his heart drop to his ass. “Okay. Shoot,” he gulped.

“Cartman.”

And Stan really couldn’t think of anyone worse. He groaned, dropping his head into his arm and unintentionally moving his hand in the process, earning a hiss from Bebe to _ not move_.

Eric Cartman. The man who had tortured him and, more importantly, his best friend, for years. The man, if you could call him that, who was just as chubby now as he was in his elementary years. The man who somehow made it work in his favor, and somehow held all the confidence in the world. The man who still loved to torment others, deriving pleasure from their pain. The man who had barely changed physically or mentally from when Stan had first met him all those years ago. The man who still acted as childish and immature as he did in 4th grade. Yet the man who had still grown so emotionally strong, capable, who understood completely how he felt and was somehow so tuned into other’s emotions.

Stan had seen significant _ emotional _ growth in Cartman, but he was still physically and mentally the same. Cartman had once been a, quite honestly, insecure and fragile little boy who cried at the drop of a hat. However, Stan now saw a truly confident man, not the faux confidence from the past. He sometimes even had his rare moments of compassion, but more often he was at most empathetic. He was still the homophobic asshole he always was. He was still the man who single-handedly outed him to the _ entire _ grade, and _ just- _

“_ Why _?” was all Stan could ask.

“You realize he’s gay, right?” Bebe asked.

It felt like Stan’s whole world had stopped. He deadpanned. “No.”

“Just ‘no’?” Kenny asked through a laugh.

Stan didn’t respond in any way. He just stared at the glimmering gloss painted on his nails.

“Haven’t you ever noticed his totally weird obsession with Kyle? He likes to torture him, but he goes to extents that the normal wouldn’t- as normal as somebody who tortures others can be.”

“Like when he was obsessed with having Kyle suck his balls, when he went on the jumbotron at that basketball game and sang to him, when he saved Kyle from the smug in San Francisco…” Bebe listed off.

“Whenever Kyle and Cartman actually agree on something, they acted like the most ferocious power couple on Earth, but whenever they fight over something the sexual tension is thick enough to cut with a knife. At least from Cartman. It’s so Goddamn obvious how much he wants him.”

That made something flare-up in Stan’s chest. He wasn’t sure what it was- maybe Kenny was right about being oblivious about his emotions -but it was a hot, uncomfortable feeling that made his stomach churn similar to the way he got before he tried to kiss a girl.

“And, y’know, I’ve fucked him before.”

Stan naturally perked up a bit, always down to hear about Kenny’s sexual adventures. “Really?”

“Sure have. And _boy,_ let me tell you, it got _wild._ He’s really not a bad fuck, honestly. I feel like he’s your only option left at this point in the game if you don’t wanna go for Kyle yet.”

Bebe crinkled her nose. She had finished Stan’s nails. “Ugh. I wouldn’t touch Cartman with a ten-foot pole.”

“See? This is why I’m the whore and you’re the spoiled one.”

“If being spoiled means that I have at least _ some _ remnants of a standard left, then I’ll take it.”

“I’ll do it,” Stan suddenly said, surprising both himself and the others.

“Really?” Kenny asked.

Stan shrugged. “I guess if I have no other options left…”

Bebe excitedly clapped her hands. “Yay! Your first guy outside of Kenny! Even though it may be Cartman, who’s almost as desperate for some dick as the three of us are and is also a fat fuck, it’s progress!”

Stan rolled his eyes. “What the fuck ever Bebe. I know you fucked Lisa Berger one time.”

Kenny snorted. “_I _ never fucked Lisa Berger.”

Bebe went red. “Shut the fuck up! We were drunk and it was one time!”

“Y’know, Bebe, I’m starting to think you’re more of a puss slut than a dick slut,” Stan pondered.

“Okay, first of all, never say that again, and second of all, girls are just prettier, bro. A lot of the guys in our class are slobs and, as I said, I have standards. Or they’re really gay and _ totally _inflexible.”

“Whatever, you dyke,” Kenny said.

“Fuck off, fag.”

A beat of silence passed through the room. However, next thing they knew, racks of laughter rattled all of their bodies. Stan lived for moments like these; the moments when he was hanging out with two of his best friends, not a single care weighing him down. Truth be told, Stan was a very stressed, sad boy. This wasn’t necessarily anything new, but Stan had felt the weight gradually lift off his shoulders ever since he started regularly seeing Kenny and Bebe and he was _ thriving _. He’d felt more alive in the past three months than he ever had in his entire life, and it was liberating. He found himself drinking less than before.

“So, Stan: Cartman, huh?” Kenny asked finally, circling back to the original conversation.

“Yes. If I’m left with no other options…”

“Yay, then we can get to work! You’ll have fun. Cartman can get pretty sexy, honestly.” Bebe crinkled her nose again. “But there’s one thing I should probably warn you about.”

“What?”

“He’s really into the BDSM scene.”

* * *

Thus Stan began his mission to woo Cartman into fucking his brains out. Which… turned out to be easier than any of them predicted.

The first step to set in motion was getting closer to Cartman again. Cartman does sit near Stan and them in the morning and lunch, but he mostly ignores everyone and sits on his phone with his Goddamn airpods in.

One Monday morning, Stan walked right up to Cartman and plopped his ass down in the seat next to him. He pulled a risky move, taking one of Cartman’s airpods right out of his ear and pocketing it. Immediately Cartman whipped his head towards Stan, glaring at him with an intensity that made his confidence falter a bit. But he hid it well, smiling brightly at Cartman like nothing was wrong. “Hey, Cartman.”

“What the fuck do you want?”

Stan shrugged, purposefully brushing his shoulder against Cartman’s in the process. He was very clearly invading Cartman’s personal space, but Cartman said nothing of it, so neither did Stan. “I just wanted to say hi. What are you watching?”

Cartman immediately shielded his phone from Stan. “None of your fucking business. Give me my airpod back.”

But instead of handing back Cartman’s airpod, he put it in his ear. Which, in hindsight, is probably disgusting, but he didn’t have time to reflect on this as he heard the voice of PewDiePie blast in his ear. “Really? PewDiePie?”

He snatched the airpod from Stan’s ear almost as soon as it entered. “I told you, it’s none of your fucking business.”

“Hold on hold on, I like Pewds.”

“As if I fucking care.”

Cartman’s face was red, from anger or embarrassment, Stan wasn’t so sure. He guessed anger, but despite his confidence, Cartman still certainly had his moments of insecurity.

“Gimme that back,” Stan said, reaching for the airpod in Cartman’s hand. Cartman, however, was already stretching his hand away, Stan’s arms no match for Cartman’s monkey limbs.

Cartman had grown to be _tall._ Like, loomed almost a good foot over Stan tall. Which, Stan wasn’t… the _ tallest _\- 5’5” is average?? -but Cartman was crazy. He had once been the shortest of the four, but Stan watched as Kenny stayed almost the same general height, Cartman and Kyle had about 500 growth spurts, and his own growth stunted at about 14 years old. Stan, also, used to be one of the tallest in his grade, but he ended up being just about average.

Not that he was complaining about half the class being tall, hunky beefcakes who could bench press him, though. Not at all.

At one point, Stan had finally snatched the airpod from Cartman’s hand, smiling as Cartman seemingly gave up. He happily plopped the bud into his ear, again forgetting to consider the cleanliness (or lack thereof) of Cartman’s ear.

For the rest of the mornings after that, Stan and Cartman would sit in the cafeteria, watching PewDiePie’s newest videos. He eventually even started to wait for Stan to arrive before watching, grumbling a _ took you long enough _ before they began watching.

They progressively got closer and closer, too; not just emotionally, but physically. They started off with a fair gap of space between their bodies, but slowly the gap closed bit by bit, day by day, until they were practically on top of each other while watching PewDiePie, their shoulders, arms, and legs constantly rubbing friction between each other.

People would often give looks, namely Kyle, but neither Stan or Cartman gave a shit, Cartman because his pride was too strong, and Stan because he was too focused on the thigh he gradually began to rub. Cartman momentarily shifted his eyes to where Stan’s hand rested, but then focused again on the screen and almost _ leaned _ into the touch, encouraging him.

One morning, Stan had walked in wearing a crop top, his first time wearing one to school that year. It showed off his belly button ring studded with a cartoon alien, and Cartman sputtered as soon as he saw him. “What the fuck? When did you get that?”

Stan grinned. That was exactly the response he was hoping for, and he gave a quick glance to Kenny and back. “I’ve had it since June. You like?”

“I- um,” Cartman’s mouth, for once, went silent, and Stan was seriously struggling to not burst into a wide grin, instead trying to play it off as a smirk. He never expected Cartman to get so flustered over a belly ring, but _ damn _ if he wasn’t living for it.

Stan decided to play the cards he was given. He reached a hand over to Cartman’s shoulder, blackly polished nails and all, and glided from one blade to the next. He sat next to Cartman, dragging his hand down along Cartman’s arm, finally looping a leg around his and intertwining their fingers.

Cartman was red in the face, noticeably shivering a few times. “Are you going to Token’s Halloween party this weekend?” he breathed, almost ragged.

Stan never would’ve anticipated having this much control over Cartman, but it felt good, so he rolled with the punches. He leaned into Cartman, against his ear, stopping there to breathe onto his shell for just a second before: “Of course. I better see you there, too.”

Cartman stared at him the rest of the day - though they shared heated glances before, the intensity and hunger in his eyes were unparalleled to the original flirty looks. Stan reciprocated his stares.

God, Saturday couldn’t come soon enough.

* * *

For Halloween, Stan and Kyle had matching costumes. They both dressed as vampires, and while Stan’s outfit was noticeably more sexual than Kyle’s, they still walked to the door with their arms looped. He felt bad for not dressing along with Kenny and Bebe- they were going as the mean girls in their Halloween costumes -and they complained that he would’ve been the perfect, mousy Karen. Kenny dressed in an almost identical outfit to the one Regina wore, just as girly, frilly, and slutty as hers had been. Bebe, on the other hand, took Gretchen’s skin-tight cat costume. The suit perfectly hugged her curves and almost had Stan questioning his sexuality again.

Hah hah, kidding.

Stan, Kyle, and Kenny rode to Token’s house in Kyle’s shitty little car. Bebe was heading to the party with some of the girls. Stan had purposely excluded inviting Cartman for a ride, wanting to wait to see him at the party. It would be a lot hotter to see Cartman at the party and be able to hop on his dick whenever he wanted instead of having to painfully and awkwardly wait in the backseat of Kyle’s car.

Upon their arrival, Stan, Kenny, and Kyle toppled over one another to get out of the car and through the front door. Stan fell behind the others as they walked ahead, admiring their costumes.

Kyle, as aforementioned, went for more of a scary approach to the vampire theme. He glued in mangily teeth to his pearly real ones, dabbing blood all around his mouth and teeth. He used toilet paper and glue to create a gnarly gash on the side of his neck, vaguely representing a bite mark. His eyes were sunken in thanks to the eyeshadow applied, his face was pale and ghoulish, his drapey clothes were torn and bloodied, and yet he _ still _ wore a fucking hat on his head. He’d never really gotten over the whole Jewfro insecurity, which Stan found to be the most ridiculous thing in the world as Stan was pretty sure his hair was a gift from the Heavens itself. Even though he was supposed to be scary, he still looked impossibly cute.

Then there was Kenny. I watched his sparkly little bunny tail bob with every step he took. His tights and one-piece perfectly hugged his body, and watching his hips sway to and fro was a bit hypnotizing. With the ridiculously high heeled boots he wore, he was now just over my height, and his bunny ears extended high into the air. Stan listened to his heels click as he watched his fluffy costume sparkle in the approaching purple and orange lights.

“Like what you see?” Kenny snickered, falling into step with Stan. Stan blinked. Rolled his eyes. “By the way, you look hot.”

“Thanks. You too.”

Stan’s costume, while being the same theme as Kyle’s, was very similar in style to Kenny’s. He slicked his hair back with gel after Kenny told him that ‘his hair looked sexy pushed back’ (which was 75% just because Regina George said that). He applied only a couple of pointy little fangs to his canines, a trickle of blood trailing from the corner of his lip, and a small bite drawn onto his neck with eyeliner. The front of his shirt was buttoned down, revealing just the tiniest bit of his fair skin. A pair of suspenders helped keep his pants up, and a cape fluttered behind him. A few patches of blood stained his white button-up.

As soon as the trio entered Token’s front doors, Stan beelined it to the kitchen. Stan was always one to drink _ hard _ at parties, and he’d been itching for some booze all day. He reached for a bottle of scotch but noticed a figure move out of the corner of his eye.

“Hey,” the hushed voice of Cartman rang out. Stan smirked, turned around, and his smile immediately faltered.

Was he seriously wearing the Goddamn Coon costume?

“Are you seriously wearing that costume right now?” Stan voiced his thoughts, scowling.

Cartman scowled back. “Yes? The Coon is a fucking hero, Stan.”

Stan poured himself a drink, rolling his eyes. “You look like a child.”

“Really? The guy in a sexy vampire costume is trying to make fun of _ my _outfit?”

Stan spun around, making eye contact with Cartman. “You think I look sexy?”

Cartman seemed to have a brain malfunction. He ripped his eyes from Stan’s gaze, only the slightest blush playing his cheeks, but it was all still there. “No. It’s just obvious that that’s what you’re going for.”

Stan chuckled, setting down his booze, but not before taking a long sip. He wrapped his arms around Cartman’s neck. “You really haven’t changed, have you?”

Cartman looked back to Stan’s eyes. “Is that good or bad?”

Stan shrugged. “Some good, some bad. But I most admire the parts of you that _ have _ changed.”

“The parts of me that have changed? Like what?”

“Like…” he began to stroke the nape of Cartman’s neck. Stan could feel a shiver run through the other boy. “How confident I’ve seen you become.” Stan’s hand moved to Cartman’s cheek, rubbing his chub in tiny little circles. “Those rare moments of compassion I see from you…” Stan looked him in the eyes.

Cartman was the first to lean in. Their lips met in a frenzy, Cartman ferociously biting and licking Stan’s lips. Stan couldn’t help but whimper, loving the pain with the pleasure of Cartman’s vicious teeth. Stan could feel him gently wipe his tongue across Stan’s fake vampire teeth. Stan hadn’t made out with many boys (yet), but from the numerous times he’d made out with Kenny, it’d never felt _ this _ passionate.

Their lips disconnect and Stan whines, chasing his lips, but Cartman pushes his hand back against Stan’s chest.

“Let’s… um,” Cartman stumbles, reaching for Stan’s hand. “Go somewhere else.”

Stan could only drunkenly nod, allowing Cartman to drag him along to find a room somewhere in Token’s house, which… ended up being a surprisingly simple task. But Stan supposed that when you hook up with someone within the first ten minutes of arriving, then there won’t be many ‘in-use’ rooms quite yet.

As soon as Cartman had closed and locked the door behind them, they were once again attacking each other’s lips. They clumsily stumbled over to the bed in the room. Stan landed on top of Cartman, and to his surprise, he suddenly felt Cartman… go limp? Not limp, exactly, but he wasn’t as aggressive in his kisses as he was before. He let Stan just completely ravish his mouth. Stan was worried that Cartman wasn’t really feeling into it anymore and, being a strong believer of complete consent, Stan pulled away to ask.

“Can you bite me?”

_Oh._

Cartman interrupted Stan with his own question, and it sent a _ something _ sensation down his spine and to his dick. It made it apparent to Stan that Cartman did indeed want to fuck, and with Cartman looking up at him with his big, brown, baby eyes, who could really say no?

Stan wasn’t really sure exactly where Cartman was expecting his bite, but Stan played it safe and bent down to his neck. With his fangs and all, he really _ did _ feel like a vampire, as he chomped down on a large section of Cartman’s pudgy neck. His fangs stayed intact for only a few seconds before they popped off his teeth and his actual canines dug into Cartman’s skin. He wasn’t really all too familiar with giving hickeys, honestly, having only received hickeys and given one to Kenny, but he knew he had to suck, trying his best to replicate what Kenny often did to his own neck.

To Stan’s delight, Cartman released the prettiest, softest moan that played in a lovely melody to his ears. “Bite. Harder,” Cartman breathed.

Stan bit harder, sucking a massive bruise into Cartman’s neck.

“Harder.”

Stan bit harder.

“Harder.”

Even harder.

“_Harder. _”

And Stan bit down so hard on Cartman’s poor, abused neck that he tasted the metallic flavor of Cartman’s blood seep into his mouth. This caused him to snap from his trance, pulling away with a smudge of real and fake blood at the corner of his lips.

“Oh fuck- dude, I’m _ so _sorry, I totally didn’t mean to bite you that hard, I just got lost in the moment and I-”

Stan cut himself off upon finally looking down at Cartman. He looked up at Stan with droopy, hazy eyes, heavy breaths floating in and out of his open mouth. Blood smeared his neck at the fresh wound. Stan came to a halting realization.

_ He’s really into the BDSM scene._

Holy _ shit. _ Cartman wasn’t the sadist… _ he was the masochist._

A smirk pulled at Stan’s lips. He wasn’t nearly expecting this, but he would be a flat-out liar if he said it wasn’t a turn on. He didn’t have any experience being the dominant one, however he _ did _ have experience being submissive, giving him a one-up into the knowledge of how bottoms liked to be treated.

“Ah… I see what’s going on,” Stan smiled down at Cartman. Cartman said nothing, just looked up with those same pleading eyes. Stan rubbed on Cartman’s bloodied wound, and Cartman sharply inhaled. “Y’know, I’ve never really done anything like this before…” Stan sweetly whispered. He adjusted himself so that he straddled Cartman’s lap, their clothed dicks rubbing against one another, drawing a mewl from the larger boy. He was already fully hard. _Cute._ “But I can tell what turns you on, and I’m willing to play along.”

Stan moved on to work on getting Cartman’s dumbass costume off. He first threw aside the mask, finally able to see the pretty pink staining his cheeks. Then he got his cape, his jacket, his t-shirt, utility belt, pants, until all that Cartman wore was his boxers and metal claws. Stan moved down to kiss Cartman, but Cartman placed a hand on his chest. Stan backed up immediately, worried he may be going too far, until he saw Cartman removing his claws and handing them to Stan.

“Put these on. Use them on me.”

Stan looked from the claws to Cartman’s face. He smiled. “Aw… is that really how you should be talking to your superior?” Stan cooed, refusing to take the claws. “Once you ask me nicely, then maybe. But I might need clearer instructions on what you’d like me to do with them.”

Stan batted his lashes at Cartman, exuding the most top _ and _ bottom energy he could, and Cartman pouted back at him. It looked like there was still some of the usual dominant Cartman left in there, eh?

Stan got off of Cartman, no longer touching any part of his body, leaving Cartman to only whine, too dick drunk to get up. “Come on. I’m waiting.”

“Fuck, okay. Please. Please, Stan, put on these metal claws. Please use them to… just fuck me up. Claw me, scratch me, draw my blood, I just want you to wreck my entire body. I don’t wanna be able to walk, stand, talk, _ breathe _ properly after tonight, just… fuck, _please,_ Stan, I’ve been thinking about this forever. _ I need you_.”

And that was all that Stan needed to hear. He took the claws from Cartman’s hands, put them on his own, hopped back on Cartman’s lap, and immediately scratched a trail from his shoulders down to his wrists. Not enough to draw blood, but enough to leave marks and force Cartman to release a wanton moan of pain and pleasure. Stan moved a hand to one of Cartman’s nipples, painfully squeezed between his metal pinchers, and Cartman’s eyes widened while he bucked his hips into Stan. Stan moaned, finally realizing just how painfully hard he’d really become. He unbuttoned his trousers, releasing some of the strain and palming himself through the fabric. His hand grazed against lace and he momentarily froze, forgetting that he wore a pair of his lacy, black thongs. He was expecting to get his brains fucked out, but now it seemed inappropriate with the sudden role change.

“Our safe word is butternut,” Stan told him after he moved a finger to his ribs. He scratched down, hard and slow over his rolls, unable to feel any bone. A tiny trail of blood glimmered on his stomach. Cartman only shuddered with a nod of his head.

Stan moved lower to finally take off Cartman’s boxers, and _ wow _ he was big. Stan’s mouth watered, and he suddenly felt disappointed that it wouldn’t be inside him. It would be in him one way or another, however, as he licked a stripe from the base up. Cartman whimpered, bucking, and Stan had to hold his hips down.

“Don’t buck,” Stan warned, “or else I’ll have to punish you.” He smiled when Cartman swallowed and nodded.

If Stan was being honest, he had _ no _idea what he would do as a form of “punishment,” but he rolled with it anyways.

Stan swallowed Cartman’s dick in one swift move, going off his many times of experience with Kenny. Cartman gasped, moaned, and Stan smiled. He loved making boys a mess like this. As he continued to bob, suck, lick, he eventually felt Cartman’s hand find Stan’s hair and pull. He wanted to stop and scold him to maintain his domineering personality, but it felt so _ good _ that he just couldn’t. He really was just a good for nothing slut and a true bottom at the core of his heart.

After a good while of cock suckage, Stan could no longer neglect his poor little dick. He took his pants off all the way, exposing his black panties, and Cartman was starstruck as he took him in.

“So… um-”

“Ride me.”

Stan smiled. Fuck _ yeah _ he would ride Eric Cartman.

He couldn’t find the energy to scold him for telling him what to do; he needed his ass filled _ now, _ and it was lucky for the both of them that he already stretched himself before coming. He quickly scissored himself with two fingers again, but otherwise he hopped on Cartman’s dick as fast as physically possible. They both moaned as loud as they possibly could, lost in the feeling of one another.

Stan began to bob, and he brought a hand to Cartman’s head. His metal claws momentarily scraped his scalp before he pulled his hair, yanking his head to the side, and Stan attacked the other side of his neck. Cartman seemed unable to control himself, pretty moans and whines and whimpers falling from his mouth in a stream and _ God _ that wasn’t a word he ever thought he’d use to describe Cartman. _ Pretty. _

Once he felt satisfied with the mangled wound on Cartman’s neck, he pulled away and focused on the movements of their hips. They worked together to find a rhythm, and once Cartman found Stan’s prostate it all became a blur of pain and pleasure. Stan dug bloody red scratches and deep purple hickeys into any patch of skin he could find and Cartman was absolutely eating it _up,_ his chubby face scrunched in pure ecstasy.

It was ferocious, wild, and when Cartman gave a high pitched moan as he began to fill Stan's ass with warm cum, that was fucking it.

Game over.

Stan's body went rigid as his orgasm racked his body. He came in stripes all over Cartman's stomach, his seed mixing with Cartman's blood. He knew he'd later feel bad about how much he'd marked Cartman's body, but right now he was too lost in the pleasure to care.

He ended up collapsing on Cartman after his orgasm had ceased. They both shared heavy breaths, and Stan's ass was _ sore _ so he had to immediately pull off of Cartman’s dick. They groaned, over-stimulated, and Stan rolled over to curl into Cartman’s side. As much as Stan loved the aggressively steamy fucks, he was also a sucker for the more tender and romantic touches. He brought an arm around Cartman’s torso, but when Cartman flinched he suddenly became conscious of the actively bleeding wounds littering Cartman’s body.

“Oh God, dude, Cartman, you’re really fucked up. I’m so sorry, let me go get some bandaging.”

If he said anything in response, Stan didn’t hear as he was already out the door - naked, mind you. When he came back he saw that Cartman hadn’t moved an inch, and he could already tell that he would require a lot of aftercare.

* * *

“Thank you… for cleaning me up,” Cartman muttered once his wounds were patched and he sat on the bed in only his underwear. His tone was uncharacteristically sweet, and it threw Stan off for a moment.

“Of course. You should take it easy now,” Stan said, patting the pillow behind him as a gesture to lie down. He lied down as well, snuggling underneath the blanket.

“Uh… what are you doing?”

“I require cuddles after sex,” Stan told, gesturing his arms out toward Cartman.

Cartman huffed with a roll of the eyes, yet still leaned down to wrap his arms around Stan in a hug. He shuffled to cover himself with the blankets. “I hope you realize this doesn’t make us a couple,” he finally said in his generally normal tone of voice.

Stan just smiled, burying his head deeper into the crook of Cartman’s neck. “I’m already about five steps ahead of you on that one, bud.”

And so they fell asleep in each other's arms, thoroughly spent and exhausted in the continuous afterglow of their orgasm… until Kenny burst the fuck in a couple of hours later and told him that they were leaving.

* * *

Date: 10/31

Entry #3

Stop It. Get Some Help.

_ I really was NOT expecting that. At this point I’m, like, a little concerned for his sanity and almost feel like I should get him some help, but does that mean I need help too bc I enjoyed it so much??? idk I’m having a bit of an existential crisis rn. _

_ Anyways, wow yea so that was really hot. When Kenny told me that he was into bdsm, I was more like… expecting him to be the sadist? But I guess fucking not. The shit he wanted me to do was… wack, but it was a turn on ngl. He had a really nice cock and I was worried he wanted me to fuck him, but NOOO he did not. He also made the cutest little goddamn expressions and noises and it just… brought out a part of me I didn’t know existed haha. Kinda scary but like ok lol _

_ Rating: 7/10, was kinda freaky in hindsight but was hot in the moment soo ?? 😜😜 _

_ \- Stan 😘 _

**Notes for the Chapter:**

> I aggressively enjoy bottom/masochist Eric Cartman almost as much as I enjoy bottom/cock slut Stan.
> 
> I really really hope you guys liked it! I know a lot of you have been asking when I would update, so I really hope this satisfied your thirst. I'm 100% unsure when the next chapter will be posted, or even who it'll be, but stay tuned everyone!
> 
> Thank you so much for reading!


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